| Identification | Back Directory | [Name]
EIPA | [CAS]
1154-25-2 | [Synonyms]
EIPA
L 593754
MH 12-43
ethylisopropylamiloride
5-(N-ETHYL-N-ISOPROPYL)AMILORIDE
AMILORIDE, 5-(N-ETHYL-N-ISOPROPYL)-
3-AMino-N-(aMinoiMinoMethyl)-6-chloro-5-[ethyl(1-Methylethyl)aMino]-
3-amino-6-chloro-N-(diaminomethylene)-5-[ethyl(isopropyl)amino]pyrazinamide
3-aMino-N-carbaMiMidoyl-6-chloro-5-(ethyl(isopropyl)aMino)pyrazine-2-carboxaMide
3-AMINO-N-(AMINOIMINOMETHYL)-6-CHLORO-5-[ETHYL(2-PROPYL)AMINO]-PYRAZINE-2-CARBOXAMIDE
3-Amino-5-[ethyl(isopropyl)amino]-6-chloro-N-(aminoiminomethyl)-2-pyrazinecarboxamide
6-Chloro-3-amino-5-[ethyl(isopropyl)amino]-N-(diaminomethylene)-2-pyrazinecarboxamide
3-Amino-5-(N-ethyl-N-isopropylamino)-6-chloro-N-(aminoiminomethyl)-2-pyrazinecarboxamide
3-Amino-N-(aminoiminomethyl)-6-chloro-5-[ethyl(1-methylethyl)amino]-2-pyrazinecarboxamide
3-amino-6-chloro-N-(diaminomethylidene)-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide
3-azanyl-N-[bis(azanyl)methylidene]-6-chloro-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide | [Molecular Formula]
C11H18ClN7O | [MDL Number]
MFCD00151710 | [MOL File]
1154-25-2.mol | [Molecular Weight]
299.76 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Solid | [Melting point ]
202-205 °C(lit.)
| [density ]
1.49±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Acetonitrile (Slightly, Heated), DMSO (Slightly), Methanol (Slightly) | [form ]
Off-white to yellow solid. | [pka]
8.67±0.46(Predicted) | [color ]
Pale Yellow to Green | [biological source]
synthetic | [Stability:]
Unstable in methanol | [InChI]
InChI=1S/C11H18ClN7O/c1-4-19(5(2)3)9-7(12)16-6(8(13)17-9)10(20)18-11(14)15/h5H,4H2,1-3H3,(H2,13,17)(H4,14,15,18,20) | [InChIKey]
QDERNBXNXJCIQK-UHFFFAOYSA-N | [SMILES]
C1(C(NC(N)=N)=O)=NC(Cl)=C(N(CC)C(C)C)N=C1N | [CAS DataBase Reference]
1154-25-2 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
Selective Na+/H+ antiporter inhibitor. Selectively enhances the excretion of sodium ions without causing an increase in excretion of potassium ions | [Description]
Sodium-hydrogen exchangers (NHE) are involved in maintaining sodium and pH balance in a variety of tissues. They are also known as sodium-hydrogen antiporters and solute carrier family 9 members. 5-(N-ethyl-N-isopropyl)-Amiloride (EIPA) is a potent inhibitor of several NHE isoforms, inhibiting NHE1, NHE2, NHE3, and NHE5 with Ki values of 0.02, 0.5, 2.4, and 0.42 μM, respectively. It less effectively inhibits NHE4 (IC50 ≥10 μM). EIPA is commonly used at a concentration of 5-10 μM to inhibit cellular HNE activity. | [Definition]
ChEBI: Ethylisopropylamiloride is a member of the class of pyrazines that is amiloride in which the amino substitutent of the pyrazine ring that is adjacent to the chloro substituent has been substituted by an ethyl group and by an isopropyl group. It has a role as an anti-arrhythmia drug, a neuroprotective agent and a sodium channel blocker. It is a member of guanidines, an aromatic amine, an organochlorine compound, a tertiary amino compound, a member of pyrazines and a monocarboxylic acid amide. It is functionally related to an amiloride. | [Biochem/physiol Actions]
Selective blocker of Na+/H+ antiport | [storage]
Store at -20°C | [References]
[1] B. MASEREEL D. L L Pochet. An overview of inhibitors of Na+/H+ exchanger[J]. European Journal of Medicinal Chemistry, 2003, 38 6: Pages 547-554. DOI: 10.1016/s0223-5234(03)00100-4
[2] S ATTAPHITAYA J E M K Park. Molecular cloning and functional expression of a rat Na+/H+ exchanger (NHE5) highly expressed in brain.[J]. The Journal of Biological Chemistry, 1999, 274 7: 4383-4388. DOI: 10.1074/jbc.274.7.4383
[3] SUNG-MIN HWANG. Intracellular acidification is associated with changes in free cytosolic calcium and inhibition of action potentials in rat trigeminal ganglion.[J]. The Journal of Biological Chemistry, 2011: 1719-1729. DOI: 10.1074/jbc.m109.090951
[4] LIN XUE. Trefoil factor 2 requires Na/H exchanger 2 activity to enhance mouse gastric epithelial repair.[J]. The Journal of Biological Chemistry, 2011: 38375-38382. DOI: 10.1074/jbc.m111.268219 |
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